2-azolylmethyl-2-phenyl-4-[benzazol-2-yloxy-or-thio-methyl]-1,3 dioxolanes and salts thereof, pharmaceutical compositions containing them and their use

Abstract

Compounds of the formula I <IMAGE> I <IMAGE> and the acid-addition salts thereof, where A=CH or N; Ar=naphthyl, thienyl or phenyl; Z=oxygen or sulfur; R1=alkyl, F or Cl; g=0-2; L=0 or 1; m=0-4; p=0 or 1; X=O, S or N-R3; R2=alkyl, alkoxy, halogen, SCH3, COC6H5, CF3, COOCH3, COOC2H5, or NO2; n=0-2; R2, under certain circumstances, is alternatively -CH=CH-CH=CH- or phenoxy are described. Processes for the preparation thereof are also described. Compounds IIIa <IMAGE> IIIa <IMAGE> are valuable intermediates for the preparation of I. The compounds I serve as antimycotics.

We claim: 
     
       1. A compound of the formula I ##STR47## in which: A is CH or N, Ar is a phenyl group which is unsubstituted or carries up to 2 substituents which are identical or different and are F, Cl, Br or C 6  H 5 ,   Z is O or, if L, m and p simultaneously are zero, is O or S,   R 1  is C 1  -C 3  -alkyl, F or Cl,   g is 0, 1 or 2,   L is 0 or 1,   m is 0, 1, 2, 3 or 4,   p is 0 or, if m does not equal 0 or if L and m are simultaneously 0, is 0 or 1,   X is O or, if m does not equal 0 or if L, m and p are simultaneously 0, is O or S,   R 2 , independently of one another, are C 1  -C 4  -alkyl, C 1  -C 4  -alkoxy, F, Cl, Br, I, SCH 3 , CO-C 6  H 5 , CF 3 , COOCH 3 , COOC 2  H 5  or NO 2 , and   n is 0, 1 or 2, and the physiologically acceptable acid-addition salt thereof.     
     
     
       2. A compound of the formula I as claimed in claim 1, in which at least one of the substituents and indices has the following meaning: A is CH or N,   Ar is a phenyl group which is substituted by 1 or 2 F or Cl atoms,   Z is O or, if L, m and p simultaneously are zero, is O or S,   R 1  is CH 3  or C 2  H 5 ,   g is 0 or 2,   L is 0 or 1,   m is 0, 1, 2 or 3,   p is 0 or, if m is 1, is 0 or 1,   x is O or, if m is 1, 2 or 3, or if L and m are simultaneously 0, or if, simultaneously, m is 0 and n is 1 or 2, is O or S,   R 2 , independently of one another, are C 1  -C 4  -n-alkyl, C 1  -C 4  -alkoxy, F, Cl or Br, and   n is 0, 1 or 2.   
     
     
       3. A compound of the formula I as claimed in claim 1, in which at least one of the substituents and indices has the following meaning: A is CH or N,   Ar is 2,4-dichlorophenyl,   Z is O,   R 1  is CH 3 ,   g is 0 or 2,   L is 0 or 1,   m is 0, 1, 2 or 3,   p is 0 or, if m is 1, is 0 or 1,   X is O or, if m is 1, 2 or 3 or if L and m are simultaneously 0, is O or S,   R 2 , independently of one another, are CH 3 , C 2  H 5 , C 1  -C 4  -alkoxy, F, Cl or Br and   n is 0, 1 or 2.   
     
     
       4. A compound of the formula I as claimed in claim 1, wherein L, m and p simultaneously are zero, or L is zero and m and p simultaneously are 1, and in each case X is O or S and n is zero or 1, and R 2  is CH 3 , C 2  H 5 , C 1  -C 4  -alkoxy, F, Cl or Br. 
     
     
       5. A compound I as claimed in claim 1, wherein the azolylmethyl radical and the piperazinophenoxymethyl group in the 4 position on the dioxolane are in the cis position. 
     
     
       6. A pharmaceutical composition having antimycotic action comprising an invert carrier material and as an active ingredient an antimycotically effective amount of a compound as claimed in claim 1. 
     
     
       7. A process for the treatment of mycoses, wherein an active amount of a compound I as claimed in claim 1, is administered together with pharmaceutically suitable excipients.